Gathering and Guiding: Four Steps to Leading Leaders with Naomi Simson

11 mins
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Gathering and Guiding: Four Steps to Leading Leaders with Naomi Simson
In this guide

Leadership is a curious thing. It's an intangible quality and notoriously hard to define. What makes someone a leader? And how do you go about gathering and guiding leaders so that together you can navigate and grow in uncertain times?

Suppose you are a company founder or a business owner; you know the importance of a unified leadership team. One of the most important aspects of being a leader is setting the vision and guiding your team in alignment with your values. When the path forward is no longer clear or straight, developing leaders who can lead is essential.

We discussed with Naomi Simson what it means to grow as a leader and will further explore four steps to building effective leadership teams.

Want more? Join Naomi's panel discussion the 29th of September for a deep dive into winning and retaining customers for your biggest Q4 ever! Register to attend here.

Step 1: Identifying as a Leader

Founder as Leader

"Often, the founder doesn't think of themselves as a leader. But that's their number one job. For them, and the people around them." - Naomi Simson

Before you can begin developing your leadership team, you need to start with yourself. Humans will often identify with multiple roles. We have different responsibilities as we interact with our families, friends, and colleagues. In some contexts, we follow or support, becoming cheerleaders, helpers or rescuers. In other contexts, we lead.

If you are a company founder, it is essential that you first and foremost identify and own your role as a leader. You are not just a business owner, a creative, or an entrepreneur. You lead leaders. Identifying as a leader means becoming great at leading yourself. It requires self-awareness and a strong vision. It means taking a step back from the everyday tasks, thinking about where you want your business to be and why, and finally, inspiring everybody to unite toward that singular cause.

The Difference between Leadership and Management

"But I am a leader!" – you say. That's excellent! Many business owners and managers have spent years leading a single project, leading a team of ten, or even leading 100 people. Still, they have not yet discovered how to inspire people outside their direct realm of influence. The terms "leader" and "manager" are often used interchangeably. Being a leader versus a manager is not a title change; it is a mindset. There are significant distinctions that set the two apart.

"Management is about nurturing the uniqueness of the individual for the good of the cause. Leadership is about uniting everybody with their unique skills. For the good of the cause." - Naomi Simson

One of the most significant factors in having a manager or leadership mindset is your ability to let go of control. You have two choices; growth or control, but you can't have both. The seminal Harvard Business Review article "Managers and Leaders: Are They Different?" (originally published in May 1977 by Abraham Zaleznik) addresses some of the challenges in creating an environment where emerging leaders can flourish.

Below is an adapted version of the original "Idea in Practice", which summarises some major differences between managers and leaders.

Reflection: Glancing at the table, what resonates with you? Are you more of a manager or a leader? In what situations do you default to a manager or rise to be a leader? Why?

Step 2: Knowing your strengths and weaknesses

In step one, you began developing your self-awareness around your manager versus leadership defaults. A critical part of identifying as a leader is the ability to lead yourself. But how does one exactly do it? Ironically, the underlying principle here is that it is not about you.

With that in mind, here are a few pointers to get you started:

Develop self-awareness

Developing self-awareness comes from listening to; those leading under you, your team members, mentors, whoever can offer valuable insight into your strengths and weaknesses.

Know you and your team's unique contribution

Knowing your strengths and your team's strengths helps you define your leadership contribution and the contribution of individuals in your team. This unique mix of personality, talent, skills, experience and networks makes each persons' leadership contribution invaluable. As they say, "the whole is greater than the sum of its parts."

Recognise you can't do everything

You are not expected to do it all and be all things to all people. Recognising your weaknesses enables you to gather a leadership team with complementary skills. It also alerts you to the potential impact you could have on your team through your blind spots.

Develop accountability structures around you

Developing accountability structures around you will assist you to have a permanent posture of listening and learning. There are many benefits to surrounding yourself with people you can trust who will call you out on bad or blind behaviour and challenge you to be a better leader.

Activity: Consider undertaking some form of strengths assessment. There are several available, such as CliftonStrengths by Gallup or the VIA Strengths Finder.
However, these assessments are just tools. Nothing beats having real people around you who can call you to account! Who are the people around you who will keep you accountable? If you don't have anyone, who could you ask right now?

Adopt a posture of learning

Leaders who stop learning, stop growing. Maintain a curious spirit, enquire, investigate, learn, grow. Whether that's about your strengths and weaknesses, your team, or the environment in which you're operating. Curiosity develops your ability to see opportunities, assess risks and perceive what emotionally connects with your customers, clients and employees.

Find your "why"

One of the critical differences between a manager and a leader, according to Zaleznik, is that a leader has a personal and active outlook. Innately we know that we are all made for a purpose. Find your reason to do what you're doing. Life is short, and having that laser-like focus on your "why" not only gives you the motivation to keep going when life gets tough but becomes the rallying vision for your team to get behind.

In this next section, we'll look at some prompters to help you find your "why".

Step 3: Gathering: The Why

Permission to Dream

The environment we're operating in is complex. It is increasingly challenging to hold onto set strategies, plans, and processes in a complex, uncertain world. With a manager mindset, this level of uncertainty can invoke minor panic or a feeling of being overwhelmed as we skip straight into the comfort of controlling through tactics and execution plans.

There are a rare few that rally behind the promise of a new process. As a leader, dreaming big casts vision, ignites the imagination, and gives space for creativity. It positions the business to identify and execute on opportunities and develops agility to bounce back from mistakes or navigate unforeseen external factors. Leaders make "safe fails" rather than "fail-safes".

Find your "why" requires you to start asking the big questions of life. However, no one said that dreaming about the future can't be fun! Give yourself and your team permission to dream. Invite everyone to contribute to the process. It's amazing what people think of when they are invited to dream about the business' ideal future – you may discover some great ideas.

Permission to dream big also gives your business that invaluable competitive advantage. Perspective.

This Dreaming Document provides some writing prompts for you to dream big. If you have either (a) rarely permitted yourself to dream and didn't know where to start or (b) want to involve your leadership team in dreaming, then this document may be a useful tool for you.

Communicating the Vision

Now that you have identified "why" you do what you do, the next step is to inspire your leadership team to gather behind this vision. You can do this by telling stories that shape the culture and spark the imagination of what is possible. Clearly articulating the vision is vital in unifying your team and giving your leaders the key messages and stories they need to inspire their teams.

When leading leaders with diverse personalities and motivators, you need to tap into their "why". Storytelling that establishes an emotional connection is a powerful tool to inspire action.

"The role of the leader is often about storytelling. It's about painting the picture. It's about showing people a better future. Remembering why you're there and your purpose." - Naomi Simson

The "why" behind your business should be the first story you communicate to your team and your customers. Naomi Simson talks about "defining your company's job". That is, tapping into the purpose that your product or service offers to your customers. Is your business providing comfort? A sense of connection? Feeling loved? Security?

Reflection exercise: Now, it is your turn to get specific. What is the story behind your "why"? What is the deeper need that your product or service can offer for them? Why should your customers, your stakeholders or your team care?

Step 4: Guiding: The What and The How

Setting the Strategy

If the vision is the why, then the strategy is the what.

Suppose you are a natural leader and your strengths are already in developing the long term vision and leading with purpose. In that case, it is even more critical for you to (1) define a strategy and (2) stay with it.

As the leader, you unite and gather your leadership team under a common vision. A strategy helps you guide your leadership team to lead others. A strategy allows people to do whole and complete work that contributes toward the vision, giving them a sense of accomplishment based on their strengths. Most importantly, as a leader, it allows you to communicate how their work directly contributes to the ultimate vision of the business, which is key to uniting people toward achieving a common goal.

There are hundreds of ways to develop a strategy and it will be a living document. The type and depth of strategy will depend on your industry cycles, business phase, and company culture. However, some of the common themes in setting a strategy include:

  1. Define a vision and your values (start with the dreaming exercise)

  2. Analyse your environment (exercises such as P.E.S.T.L.E or S.W.O.T can be helpful)

  3. Identify where the opportunities are and associated risks

  4. Identify which ones you want to go for and which ones you won't (test these against your vision and values)

  5. Figure out when, where, how to go for those opportunities (and who will do it) and what the trade-offs are

  6. Set goals, measure, communicate

Reflection: Consider what your business is doing now. What trajectory is it on, and where will it be in two years or even ten years?
Which activities, projects or products are most strongly aligned to your vision? Which ones are not (or no longer) contributing to your vision?

Establishing your Values

Values are all about what is most important to you and the business. They are the real mountain on which your business will either thrive or die. The values are CORE to what makes your business unique because they determine the how.

Enacted values are categorically different from espoused values. It is essential to uncover the basic assumptions behind your business' enacted values before implementing any change.

Develop observation skills within your leadership team by asking them to be your observers and listening posts. It would be helpful to observe your business in various circumstances.

Action: What stories are being told about the organisation? What values are being expressed in customer interactions, employee onboarding or marketing activities? What is not being done?

There is no shortcut. To close the gap between enacted values and espoused values, you need to go right to the roots and challenge the basic assumptions. Remember the accountability structure that you put in place earlier on? This is where their wisdom can really shine.


When developing your leadership team, people will gather under the vision, the strategy will guide them, but ultimately, they will go based on their values.

First, identify as a leader. If you want to lead leaders, it starts with leading yourself. Define your why, know your what and, above all, interrogate your how. Second, know your strengths and weaknesses. This self-awareness allows you to articulate your unique leadership contribution and understand where you need to build a fantastic team around you.

From this point, you can develop a solid leadership team from this place of clarity who can lead and inspire others to gather under a shared vision. As you navigate uncertain times, dream together, communicate together, and reshape the future together.

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